Tropane alkaloid
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Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure.[1] Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural associations.[2][3][4][5][6][7] Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants.
Classification
Anticholinergics
Anticholinergic drugs[8] and deliriants:[9][10][11][12][13]
- Atropine, racemic hyoscyamine, from the deadly nightshade (Atropa belladonna)
- Hyoscyamine, the levo-isomer of atropine, from henbane (Hyoscyamus niger), mandrake (Mandragora officinarum) and the sorcerers' tree (Latua pubiflora).
- Scopolamine, from henbane and Datura species (Jimson weed)
All three acetylcholine-inhibiting chemicals can also be found in the leaves, stems, and flowers in varying, unknown amounts in Brugmansia (angel trumpets), a relative of Datura. The same is also true of many other plants belonging to subfamily Solanoideae of the Solanaceae, the alkaloids being concentrated particularly in the leaves and seeds. However, the concentration of alkaloids can vary greatly, even from leaf to leaf and seed to seed.[14][15]
Stimulants
Stimulants and cocaine-related alkaloids:[10][16]
- Cocaine, from coca plant (Erythroxylum coca)
- Ecgonine, a precursor and metabolite of cocaine
- Benzoylecgonine, a metabolite of cocaine
- Hydroxytropacocaine, from coca plant (Erythroxylum coca)
- Methylecgonine cinnamate, from coca plant (Erythroxylum coca)
Others
- Catuabines, found in catuaba, an infusion or dry extract made from Erythroxylum vaccinifolium[10][12][13]
- Scopine[10][12][13]
Synthetic analogs of tropane alkaloids also exist, such as the phenyltropanes. They are not considered to be alkaloids per definition.
Biosynthesis
The biosynthesis of the tropane alkaloids have attracted intense interest because of their high physiological activity as well as the presence of the bicyclic tropane core.[17]
References
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- ^ Page Module:Citation/CS1/styles.css has no content.Hesse M (2002). Alkaloids: Nature's Curse or Blessing?. Weinheim: Wiley-VCH. p. 304. ISBN 978-3-906390-24-6.
- ^ Page Module:Citation/CS1/styles.css has no content.Ryzik M (10 June 2007). "Cocaine: Hidden in Plain Sight". The New York Times. Archived from the original on 11 August 2017. Retrieved 18 May 2017.
- ^ Page Module:Citation/CS1/styles.css has no content."The Buyers – A Social History of America's Most Popular Drugs". FRONTLINE. PBS. Archived from the original on 14 May 2017. Retrieved 18 May 2017.
- ^ Page Module:Citation/CS1/styles.css has no content.Anderson L. "Devil's Breath: Urban Legend or the World's Most Scary Drug?". Drugs.com. Retrieved 9 July 2019.
- ^ Page Module:Citation/CS1/styles.css has no content.Fatur K (June 2020). ""Hexing Herbs" in Ethnobotanical Perspective: A Historical Review of the Uses of Anticholinergic Solanaceae Plants in Europe". Economic Botany. 74 (2): 140–158. Bibcode:2020EcBot..74..140F. doi:10.1007/s12231-020-09498-w. ISSN 0013-0001. S2CID 220844064.
- ^ Page Module:Citation/CS1/styles.css has no content.Rätsch C (2005). The Encyclopedia of Psychoactive Plants: Ethnopharmacology and Its Applications. Park Street Press. ISBN 978-0-89281-978-2.
- ^ Page Module:Citation/CS1/styles.css has no content.Grynkiewicz G, Gadzikowska M (2008). "Tropane alkaloids as medicinally useful natural products and their synthetic derivatives as new drugs". Pharmacological Reports. 60 (4): 439–463. PMID 18799813.
- ^ Page Module:Citation/CS1/styles.css has no content.Volgin AD, Yakovlev OA, Demin KA, Alekseeva PA, Kyzar EJ, Collins C, et al. (16 October 2018). "Understanding Central Nervous System Effects of Deliriant Hallucinogenic Drugs through Experimental Animal Models". ACS Chemical Neuroscience. 10 (1): 143–154. doi:10.1021/acschemneuro.8b00433. PMID 30252437. S2CID 52824516.
- ^ a b c d Page Module:Citation/CS1/styles.css has no content.Kohnen-Johannsen KL, Kayser O (February 2019). "Tropane Alkaloids: Chemistry, Pharmacology, Biosynthesis and Production". Molecules. 24 (4). Basel, Switzerland: 796. doi:10.3390/molecules24040796. PMC 6412926. PMID 30813289.
- ^ Page Module:Citation/CS1/styles.css has no content.Sweta VR, Lakshmi T (2015). "Pharmacological profile of tropane alkaloids". Journal of Chemical and Pharmaceutical Research. 7 (5): 117–119.
- ^ a b c Page Module:Citation/CS1/styles.css has no content.Gong H, He P, Lan X, Zeng L, Liao Z (2022). "Biotechnological Approaches on Engineering Medicinal Tropane Alkaloid Production in Plants". Frontiers in Plant Science. 13 924413. doi:10.3389/fpls.2022.924413. PMC 9201383. PMID 35720595.
- ^ a b c Page Module:Citation/CS1/styles.css has no content.Christen P, Bieri S, Berkov S (2013). "Methods of analysis: Tropane alkaloids from plant origin.". Natural products. pp. 1009–1048. doi:10.1007/978-3-642-22144-6_35. ISBN 978-3-642-22144-6.
- ^ Page Module:Citation/CS1/styles.css has no content.Hawkes JG, Lester RN, Skelding AD, eds. (1979). The Biology and Taxonomy of the Solanaceae. Linnean Society Symposium Series. Vol. 7. Academic Press for the Linnean Society of London. ISBN 978-0-12-333150-2.
- ^ Page Module:Citation/CS1/styles.css has no content.Eich E (2008). Solanaceae and Convolvulaceae: Secondary Metabolites – Biosynthesis, Chemotaxonomy, Biological and Economic Significance (A Handbook). Berlin Heidelberg: Springer-Verlag. ISBN 978-3-540-74541-9.
- ^ Page Module:Citation/CS1/styles.css has no content.Roque Bravo R, Faria AC, Brito-da-Costa AM, Carmo H, Mladěnka P, Dias da Silva D, et al. (April 2022). "Cocaine: An Updated Overview on Chemistry, Detection, Biokinetics, and Pharmacotoxicological Aspects including Abuse Pattern". Toxins. 14 (4): 278. doi:10.3390/toxins14040278. PMC 9032145. PMID 35448887.
- ^ Page Module:Citation/CS1/styles.css has no content.Leete E (Aug 1990). "Recent Developments in the Biosynthesis of the Tropane Alkaloids1". Planta Medica. 56 (4): 339–352. Bibcode:1990PlMed..56..339L. doi:10.1055/s-2006-960979. PMID 2236285.
